Partially fluorinated alkanols having a tertiary structure

Abstract

Novel partially fluorinated alkanes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.

Description

FIELD OF THE INVENTION

This invention relates to novel partially fluorinated alkanols having a tertiary structure and 4 to 9 carbon atoms. These compounds are useful in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing and dry cleaning.

BACKGROUND OF THE INVENTION

Cold cleaning is an application where numerous solvents are used. In most cold cleaning applications, the soiled part is either immersed in the fluid or wiped with rags or similar objects soaked in solvents and allowed to air dry.

In cold cleaning applications, the use of the aerosol packaging concept has long been found to be a convenient and cost effective means of dispensing solvents. Aerosol products utilize a propellant gas or mixture of propellant gases, preferably in a liquefied gas rather than a compressed gas state, to generate sufficient pressure to expel the active ingredients, i.e. product concentrates such as solvents, from the container upon opening of the aerosol valve. The propellants may be in direct contact with the solvent, as in most conventional aerosol systems, or may be isolated from the solvent, as in barrier-type aerosol systems.

Vapor degreasing and solvent cleaning with fluorocarbon based solvents have found widespread use in industry for the degreasing and otherwise cleaning of solid surfaces, especially intricate parts and difficult to remove soils.

In its simplest form, vapor degreasing or solvent cleaning consists of exposing a room temperature object to be cleaned to the vapors of a boiling solvent. Vapors condensing on the object provide clean distilled solvent to wash away grease or other contamination. Final evaporation of solvent from the object leaves behind no residue as would be the case where the object is simply washed in liquid solvent.

For soils which are difficult to remove, where elevated temperature is necessary to improve the cleaning action of the solvent, or for large volume assembly line operations where the cleaning of metal parts and assemblies must be done efficiently and quickly, the conventional operation of a vapor degreaser consists of immersing the part to be cleaned in a sump of boiling solvent which removes the bulk of the soil, thereafter immersing the part in a sump containing freshly distilled solvent near room temperature, and finally exposing the part to solvent vapors over the boiling sump which condense on the cleaned part. In addition, the part can also be sprayed with distilled solvent before final rinsing.

Vapor degreasers suitable in the above-described operations are well known in the art. For example, Sherliker et al. in U.S. Pat. No. 3,085,918 disclose such suitable vapor degreasers comprising a boiling sump, a clean sump, a water separator, and other ancillary equipment.

Chlorofluorocarbon solvents, such as trichlorotrifluoroethane, have attained widespread use in recent years as effective, nontoxic, and nonflammable agents useful in degreasing applications and other solvent cleaning applications. One isomer of trichlorotrifluoroethane is 1,1,2-trichloro-1,2,2-trifluoroethane (known in the art as CFC-113). CFC-113 has a boiling point of about 47.degree. C. and has been found to have satisfactory solvent power for greases, oils, waxes and the like. It has therefore found widespread use for cleaning electric motors, compressors, heavy metal parts, delicate precision metal parts, printed circuit boards, gyroscopes, guidance systems, aerospace and missile hardware, aluminum parts and the like.

Another commonly used solvent is chloroform (known in the art as HCC-20) which has a boiling point of about 63.degree. C. Perchloroethylene is a commonly used dry cleaning and vapor degreasing solvent which has a boiling point of about 121.degree. C. These compounds are disadvantageous for use as solvents because they are toxic; also, chloroform causes liver damage when inhaled in excess.

Although chlorine is known to contribute to the solvency capability of a compound, fully halogenated chlorofluorocarbons and hydrochlorocarbons are suspected of causing environmental problems in connection with the earth's protective ozone layer. Thus, the art is seeking new compounds which do not contribute to environmental problems but yet provide the solvency properties of CFC-113. From an environmental standpoint, partially fluorinated alkanols are of interest because they are considered to be stratospherically safe substitutes for the currently used fully halogenated chlorofluorocarbons.

It is an object of this invention to provide novel partially fluorinated alkanols which are liquid at room temperature and which are useful as solvents for use in vapor degreasing, cold cleaning, and other solvent cleaning applications including defluxing applications and dry cleaning.

Another object of the invention is to Provide novel environmentally acceptable solvents for use in the aforementioned applications.

Other objects and advantages of the invention will become apparent from the following description.

DETAILED DESCRIPTION OF THE INVENTION

We have found a novel class of alkanols which we believe have good solvency characteristics. The present novel compounds are of the Formula: ##STR2## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2 --, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms.

Because C in the Formula above has three alkyl groups thereon, these novel compounds have a tertiary structure. We believe that this tertiary structure provides good solvency power. When the present compounds are used as solvents, the compounds have good solvency power for polar contaminants such as polyols and amines and for nonpolar contaminants including hydrocarbons such as mineral oil. We also believe that these novel compounds have boiling points which are comparable to those of currently used solvents.

Preferably, R' in the Formula above is selected the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, CH.sub.3, CF.sub.3 CF.sub.2 --, CF.sub.3 (CF.sub.2).sub.2 --, CF.sub.3 CF.sub.2 CHF--, CF.sub.3 CF.sub.2 CH.sub.2 --, CF.sub.3 CHF--, CF.sub.3 (CHF).sub.2 --, CF.sub.3 CHFCF.sub.2 --, CF.sub.3 CHFCH.sub.2 --, CF.sub.3 CH.sub.2 --, CF.sub.3 (CH.sub.2).sub.2 --, CF.sub.3 CH.sub.2 CF.sub.2 --, CF.sub.3 CH.sub.2 CHF--, CHF.sub.2 CF.sub.2 --, CHF.sub.2 (CF.sub.2).sub.2 --, CHF.sub.2 CF.sub.2 CHF--, CHF.sub.2 CF.sub.2 CH.sub.2 --, CHF.sub.2 CHF--, CHF.sub.2 (CHF).sub.2 --, CHF.sub.2 CHFCF.sub.2 --, CHF.sub.2 CHFCH.sub.2 --, CHF.sub.2 CH.sub.2 --, CHF.sub.2 (CH.sub.2).sub.2 --, CHF.sub.2 CH.sub.2 CF.sub.2 --, CHF.sub.2 CH.sub.2 CHF--, CH.sub.2 FCF.sub.2 --, CH.sub.2 F(CF.sub.2).sub.2 --, CH.sub.2 FCF.sub.2 CHF-- , CH.sub.2 FCF.sub.2 CH.sub.2 --, CH.sub.2 FCHF--, CH.sub.2 F(CHF).sub.2 --, CH.sub.2 FCHFCF.sub.2 --, CH.sub.2 FCHFCH.sub.2 --, CH.sub.2 FCH.sub.2 --, CH.sub.2 F(CH.sub.2).sub.2 --, CH.sub.2 FCH.sub.2 CF.sub.2 --, CH.sub.2 FCH.sub.2 CHF--, CH.sub.3 CF.sub.2 --, CH.sub.3 (CF.sub.2).sub.2 --, CH.sub.3 CF.sub.2 CHF--, CH.sub.3 CF.sub.2 CH.sub.2 --, CH.sub.3 CHF--, CH.sub.3 (CHF).sub.2 --, CH.sub.3 CHFCF.sub.2 --, CH.sub.3 CHFCH.sub.2 --, CH.sub.3 CH.sub.2 --, CH.sub.3 (CH.sub.2).sub.2 --, CH.sub.3 (CH.sub.2).sub.3 --, CH.sub.3 CH.sub.2 CF.sub.2 --, CH.sub.3 (CH.sub.2).sub.2 CF.sub.2 --, CH.sub.3 (CH.sub.2).sub.3 CF.sub.2 --, CH.sub.3 CH.sub.2 (CF.sub.2).sub.2 --, CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2 --, and CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2 --.

In the Formula above, when one R is CF.sub.3, the other R is CHF.sub.2, and R' is CH.sub.3, the compound is 2-methyl-1,1,1,3,3-pentafluoro-2-propanol. When one R is CF.sub.3, the other R is CHF.sub.2, and R' is CF.sub.3 CF.sub.2 --, the compound is 2-difluoromethyl-1,1,1,3,3,4,4,4-octafluoro-2-butanol. When one R is CF.sub.3, the other R is CHF.sub.2, and R' is CH.sub.3 CF.sub.2 --, the compound is 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-butanol. When one R is CF.sub.3, the other R is CHF.sub.2, and R' is CH.sub.3 (CF.sub.2).sub.2 --, the compound is 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol. When one R is CF.sub.3, the other R is CHF.sub.2, and R' is CH.sub.3 CH.sub.2 CF.sub.2 --, the compound is 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol. When one R is CF.sub.3, the other R is CHF.sub.2, and R' is CH.sub.3 CH.sub.2 (CF.sub.2 ).sub.2 --, the compound is 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.

When one R is CF.sub.3, the other R is CH.sub.2 F, and R' is CH.sub.3, the compound is 2-methyl-1,1,1,3-tetrafluoro-2-propanol. When one R is CF.sub.3, the other R is CH.sub.2 F, and R' is CHF.sub.2 CHF--, the compound is 2-fluoromethyl-1,1,1,3,4,4-hexafluoro-2-butanol. When one R is CF.sub.3, the other R is CH.sub.2 F, and R' is CH.sub.3 CF.sub.2 --, the compound is 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-butanol. When one R is CF.sub.3, the other R is CH.sub.2 F, and R' is CH.sub.3 (CF.sub.2).sub.2 --, the compound is 2fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol. When one R is CF.sub.3, the other R is CH.sub.2 F, and R' is CH.sub.3 CH.sub.2 CF.sub.2 --, the compound is 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol. When one R is CF.sub.3, the other R is CH.sub.2 F, and R' is CH.sub.3 CH.sub.2 (CF.sub.2).sub.2 --, the compound is 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.

When one R is CF.sub.3, the other R is CH.sub.3 CF.sub.2 --, and R' is CH.sub.3, the compound is 2-methyl-1,1,1,3,3-pentafluoro-2-butanol. When one R is CHF.sub.2, the other R is CH.sub.2 F, and R' is CH.sub.3, the compound is 2-methyl-1,1,3-trifluoro-2-propanol.

It is believed that the present novel compounds may be prepared by adapting known methods for preparing known alkanols coupled with the knowledge of one skilled in the art. For example, 2-methyl-1,1,1,3,3-pentafluoro-2-propanol may be prepared by reacting commercially available 1,1,1-trifluoro-2-propanone with CF.sub.2 carbene to form 2-trifluoromethyl-1,1-difluoro-1-propene which may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,1,3,3-pentafluoro-2-propanol.

To prepare 2-difluoromethyl-1,1,1,3,3,4,4,4-octafluoro-2-butanol, caesium fluoride and perfluoro-3-methylbut-1-ene may be reacted in moist sulpholan as taught by Robert N. Haszeldine et al., "Fluoro-olefin Chemistry. Part 11. Some Reactions of Perfluoro-3-methylbut-1-ene under Ionic and Free-radical Conditions", J. Chem. Soc. 565 (1979) to form 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane. The 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3,4,4,4-octafluoro-2-butanol.

As another example, 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be dehydrogenated to form 3,3-difluoro-1-butene. CF.sub.3 may then be added to the 3,3-difluoro-1-butene to form 2-trifluoromethyl-1,3,3-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-butene. The 2-trifluoromethyl-1,3,3-trifluoro-1-butene may then be reacted with hydrogen fluoride to form 2-difluoromethyl-1,1,1,3,3,3-hexafluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-butene which may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-butanol.

As another example, 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol may be prepared by fluorinating commercially available 2,3-pentanedione to form 2,2,3,3-tetrafluoropentane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-pentene. CF.sub.3 may then be added to the 3,3,4,4-tetrafluoro-1-pentene to form 2-trifluoromethyl-1,3,3,4,4-pentafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoro-1-pentene which may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol.

As another example, 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating commercially available 3-pentanone to form 3,3-difluoropentane which may then be dehydrogenated to form 3,3-difluoro-1-pentene. CF.sub.3 may then be reacted with the 3,3-difluoro-1-pentene to form 2-trifluoromethyl-1,3,3-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-pentene. The 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3-tetrafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-pentene which may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol.

As another example, 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol may be prepared by fluorinating commercially available 3,4-hexanedione to form 3,3,4,4-tetrafluorohexane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-hexene. CF.sub.3 may then be added to the 3,3,4,4-tetrafluoro-1-hexene to form 2-trifluoromethyl-1,3,3,4,4-pentafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoro-1-hexene which may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.

As another example, 2-methyl-1,1,1,3-tetrafluoro-2-propanol may be prepared by reacting commercially available methacrylic acid with hydrogen fluoride to form 2-methyl-3-fluoropropanoic acid which may then be fluorinated to form 2-methyl-1,1,1,3-tetrafluoropropane. The 2-methyl-1,1,1,3-tetrafluoropropane may then be dehydrogenated and reacted with sulfuric acid and then water to form 2-methyl-1,1,1,3-tetrafluoro-2-propanol.

As another example, 2-fluoromethyl-1,1,1,3,4,4-hexafluoro-2-butanol may be prepared by fluorinating commercially available 3-chloropropionic acid to form 1,1,1,3-tetrafluoropropane which may then be reacted with CHF.sub.2 CF carbene to form 2-fluoromethyl-1,1,1,3,4,4-hexafluorobutane. The 2-fluoromethyl-1,1,1,3,4,4-hexafluorobutane may then be dehydrogenated and reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,4,4-hexafluoro-2-butanol.

As another example, 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be dehydrogenated to form 3,3-difluoro-1-butene. CF.sub.3 may then be added to the 3,3-difluoro-1-butene to form 2-trifluoromethyl-1,3,3-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-butene. The 2-trifluoromethyl-1,3,3-trifluoro-1-butene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-butanol.

As another example, 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol may be prepared by fluorinating commercially available 2,3-pentanedione to form 2,2,3,3-tetrafluoropentane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-pentene. CF.sub.3 may then be added to the 3,3,4,4-tetrafluoro-1-pentene to form 2-trifluoromethyl-1,3,3,4,4-pentafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol.

As another example, 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating 3-pentanone to form 3,3-difluoropentane which may then be dehydrogenated to form 3,3-difluoro-1-pentene. CF.sub.3 may then be reacted with the 3,3-difluoro-1-pentene to form 2-trifluoromethyl-1,3,3-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-pentene. The 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol.

As another example, 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol may be prepared by fluorinating commercially available 3,4-hexanedione to form 3,3,4,4-tetrafluorohexane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-hexene. CF.sub.3 may then be added to the 3,3,4,4-tetrafluoro-1-hexene to form 2-trifluoromethyl-1,3,3,4,4-pentafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.

As another example, 2-methyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-methyl-1-buten-3-yne to form 2-methyl-1,2,3,4-tetrafluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,2,3,3,4-pentafluorobutane. The 2-methyl-1,2,3,3,4-pentafluorobutane may then be dehalogenated to form 3-methyl-2,3,4-trifluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,2,3,3-tetrafluorobutane. The 2-methyl-1,2,3,3-tetrafluorobutane may then be dehalogenated to form 2-methyl-1,3,3-trifluoro-1-butene which may then be fluorinated to form 2-methyl-1,1,2,3,3-pentafluorobutane. The 2-methyl-1,1,2,3,3-pentafluorobutane may then be dehydrohalogenated to form 2-methyl-1,1,3,3-tetrafluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,1,1,3,3-pentafluorobutane. The 2-methyl-1,1,1,3,3-pentafluorobutane may then be dehydrogenated and then reacted with sulfuric acid and water to form 2-methyl-1,1,1,3,3-pentafluoro-2-butanol.

As another example, 2-methyl-1,1,3-trifluoro-2-propanol may be prepared by reacting commercially available fluoroacetone with a CF.sub.2 carbene to form 2-methyl-1,1,3-trifluoro-1-propene which may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,3-trifluoro-2-propanol.

Preferably, each R in the Formula above is the same. When each R is CHF.sub.2 and R' is CF.sub.3, the compound is 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-propanol. When each R is CHF.sub.2 and R' is CHF.sub.2, the compound is 2-difluoromethyl-1,1,3,3-tetrafluoro-2-propanol. When each R is CHF.sub.2 and R' is CH.sub.2 F, the compound is 2-fluoromethyl-1,1,3,3-tetrafluoro-2-propanol. When each R is CHF.sub.2 and R' is CH.sub.3, the compound is 2-methyl-1,1,3,3-tetrafluoro-2-propanol. When each R is CH.sub.2 F and R' is CHF.sub.2, the compound is 2-fluoromethyl-1,1,3-trifluoro-2-propanol. When each R is CH.sub.2 F and R' is CH.sub.2 F, the compound is 2-fluoromethyl-1,3-difluoro-2-propanol.

As another preparation example, 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-propanol may be prepared by fluorinating commercially available 1,1,1,3,3-pentachloro-2-propanone to form 1,1,1,3,3-pentafluoro-2-propanone which may then be reacted with CF.sub.2 carbene to form 2-difluoromethyl-1,1,3,3,3-tetrafluoro-1-propene. The 2-difluoromethyl-1,1,3,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-propanol.

As another example, the 2-difluoromethyl-1,1,3,3-tetrafluoro-2-propanol may be prepared by fluorinating commercially available 1,1,3-trichloro-2-propanone to form 1,1,3-trifluoro-2-propanone which may then be reacted with CF.sub.2 carbene to form 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene. The 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene may then be hydrogenated to form 2-fluoromethyl-1,1,3,3-tetrafluoropropane. The 2-fluoromethyl-1,1,3,3-tetrafluoropropane may then be dehydrogenated to form 2-difluoromethyl-1,3,3-trifluoro-1-propene which may then be reacted with hydrogen fluoride to form 2-difluoromethyl-1,1,3,3-tetrafluoropropane. The 2-difluoromethyl-1,1,3,3-tetrafluoropropane may then be dehydrogenated and then reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,3,3-tetrafluoro-2-propanol.

As another example, 2-fluoromethyl-1,1,3,3-tetrafluoro-2-propanol may be prepared by fluorinating commercially available 1,1,3-trichloro-2-propanone to form 1,1,3-trifluoro-2-propanone which may then be reacted with CF.sub.2 carbene to form 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene. The 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,3,3-tetrafluoro-2-propanol.

As another example, 2-methyl-1,1,3,3-tetrafluoro-2-propanol may be prepared by fluorinating commercially available 1,1-dichloro-2-propanone to form 1,1-difluoro-2-propanone which may then be reacted with CF.sub.2 carbene to form 2-methyl-1,1,3,3-tetrafluoro-1-propene. The 2-methyl-1,1,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,3,3-tetrafluoro-2-propanol.

As another example, the 2-fluoromethyl-1,1,3-trifluoro-2-propanol may be prepared by oxidizing commercially available 1,3-difluoro-2-propanol to 1,3-difluoro-2-propanone which may then be reacted with a CF.sub.2 carbene to form 2-fluoromethyl-1,1,3-trifluoro-1-propene. The 2-fluoromethyl-1,1,3-trifluoro-1-propene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,3-trifluoro-2-propanol.

As another example, the 2-fluoromethyl-1,3-difluoro-2-propanol may be prepared by oxidizing commercially available 1,3-difluoro-2-propanol to 1,3-difluoro-2-propanone which may then be reacted with a CF.sub.2 carbene to form 2-fluoromethyl-1,1,3-trifluoro-1-propene. The 2-fluoromethyl-1,1,3-trifluoro-1-propene may then be hydrogenated to form 2-fluoromethyl-1,1,3-trifluoropropane. The 2-fluoromethyl-1,1,3-trifluoropropane may then be dehydrohalogenated to form 2-fluoromethyl-1,3-difluoro-1-propene which may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,3-difluoro-2-Propanol.

More preferably, each R in the Formula above is CF.sub.3. When R is CF.sub.3 CF.sub.2 CHF--, the compound is 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol. To prepare 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol, commercially available hexafluoropropene may be oligomerized with commercially available trimethylamine in a dipolar aprotic solvent such as commercially available tetrahydrofuran to provide (CF.sub.3).sub.2 C:CFCF.sub.2 CF.sub.3 as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications, 1444 (1970); the (CF.sub.3).sub.2 C:CFCF.sub.2 CF.sub.3 may then be reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol.

Most preferably, each R is CF.sub.3 and R' is selected from the group consisting of CHF.sub.2, CH.sub.3, CF.sub.3 CF.sub.2 CHF--, CF.sub.3 CHF--, CF.sub.3 CH.sub.2 --, CHF.sub.2 CH.sub.2 --, CH.sub.3 CF.sub.2 --, CH.sub.3 CH.sub.2 CF.sub.2 --, CH.sub.3 (CH.sub.2).sub.2 CF.sub.2 --, CH.sub.3 CH.sub.2 --, and CH.sub.3 (CH.sub.2).sub.2 --. The names of the preceding preferred hydrofluorocarbons are 2-difluoromethyl-1,1,1,3,3,3-hexafluoro-2-propanol; 2-methyl-1,1,1,3,3,3-hexafluoro-2-propanol; 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol; 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluoro-2-butanol: 2-trifluoromethyl-1,1,1,4,4,4-hexafluoro-2-butanol; 2-trifluoromethyl-1,1,1,4,4-pentafluoro-2-butanol; 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-butanol; 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol: 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-hexanol; 2-trifluoromethyl-1,1,1-trifluoro-2-butanol; and 2-trifluoromethyl-1,1,1-trifluoro-2-pentanol.

As another example, 2-difluoromethyl-1,1,1,3,3,3-hexafluoro-2-propanol may be prepared by treating commercially available hexafluoropropene with hydrogen fluoride as taught by commonly assigned U.K. Patent 902,590 to form 1,1,1,2,3,3,3-heptafluoropropane. The 1,1,1,2,3,3,3-heptafluoropropane may then be heated at 475.degree.-700.degree. C. in the presence of activated carbon as taught by commonly assigned U.S. Pat. No. 2,981,763 which is incorporated herein by reference to form 2-trifluoromethyl-1,1,1,3,3,3-hexafluoropropane or nonafluoroisobutane. The nonafluoroisobutane may then be treated with commercially available benzoyl chloride in the presence of commercially available triethylamine as taught by B. L. Dyatkin et al., "The Perfluoro-t-butyl Anion in the Synthesis of Organofluorine Compounds", Russian Chemical Reviews 45(7). 607 (1976) to form perfluoroisobutene. The perfluoroisobutene may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3,3-hexafluoro-2-propanol.

As another example, 2-methyl-1,1,1,3,3,3-hexafluoro-2-propanol may be prepared by reacting commercially available hexafluoropropene with elemental sulfur and commercially available potassium fluoride in commercially available dimethylformamide under substantially atmospheric pressure and at temperatures between 25.degree.-100.degree. C. as taught by commonly assigned U.S. Pat. No. 4,326,068 which is incorporated herein by reference to form hexafluorothioacetone dimer. The hexafluorothioacetone dimer may then be reacted with commercially available formaldehyde as taught by commonly assigned U.S. Pat. No. 4,367,349 which is incorporated herein by reference to form hexafluoroisobutylene. The hexafluoroisobutylene may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,1,3,3,3-hexafluoro-2-propanol.

To prepare 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol, commercially available hexafluoropropene may be oligomerized with commercially available trimethylamine in a dipolar aprotic solvent such as commercially available tetrahydrofuran to provide (CF.sub.3).sub.2 C:CFCF.sub.2 CF.sub.3 which is then reacted with commercially available hydrogen fluoride to yield 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications, 1444 (1970). The 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol.

As another example, 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluoro-2-butanol may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., "Addition of Free Radicals to Unsaturated Systems. Part XX. The Direction of Radical Addition of Heptafluoro-2-iodopropane to Vinyl Fluoride, Trifluoroethylene, and Hexafluoropropene", J. C. S. Perkin I, 574 (1973) to form a product which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,4,4,4-octafluorobutane. The 2-trifluoromethyl-1,1,1,2,3,4,4,4-octafluorobutane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1,4,4,4-hexafluoro-2-butanol may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., supra, to form a product which may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,1,2,4,4,4-hexafluorobutane which may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,4,4,4-hexafluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1,4,4-pentafluoro-2-butanol may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., supra, to form a product which may then be hydrogenated to form 2-trifluoromethyl-1,1,1,2,4,4-hexafluorobutane which may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,4,4-pentafluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be dehydrogenated to form 3,3-difluoro-1-butene. CF.sub.3 may then be added to the 3,3-difluoro-1-butene to form 2-trifluoromethyl-1,3,3-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-butene. The 2-trifluoromethyl-1,3,3-trifluoro-1-butene may then be reacted with hydrogen fluoride to form 2-difluoromethyl-1,1,1,3,3-pentafluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-butene which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,3-hexafluorobutane. The 2-trifluoromethyl-1,1,1,2,3,3-hexafluorobutane is then hydrolyzed to form 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating commercially available 3-pentanone to form 3,3-difluoropentane which may then be dehydrogenated to form 3,3-difluoro-1-pentene. CF.sub.3 may then be reacted with the 3,3-difluoro-1-pentene to form 2-trifluoromethyl-1,3,3-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-pentene. The 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3-tetrafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-pentene which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,3-hexafluoropentane. The 2-trifluoromethyl-1,1,1,2,3,3-hexafluoropentane is then hydrolyzed to form 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol.

As another example, 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-hexanol may be prepared by fluorinating commercially available 3-hexanone to form 3,3-difluorohexane which may then be dehydrogenated to form 3,3-difluoro-2-hexene. CF.sub.3 may then be reacted with the 3,3-difluoro-2-hexene to form 2-trifluoromethyl-1,3,3-trifluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-hexene. The 2-trifluoromethyl-1,3,3-trifluoro-1-hexene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3-tetrafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-hexene which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,3-hexafluorohexane. The 2-trifluoromethyl-1,1,1,2,3,3-hexafluorohexane may then be hydrolyzed to form 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-hexanol.

As another example, 2-trifluoromethyl-1,1,1-trifluoro-2-butanol may be prepared by fluorinating commercially available butyraldehyde to form 1,1-difluorobutane which may then be dehydrogenated to form 1,1-difluoro-1-butene. CF.sub.3 may then be reacted with the 1,1-difluoro-1-butene to form 2-trifluoromethyl-1,1,1-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,1-trifluoro-2-butene. The 2-trifluoromethyl-1,1,1-trifluoro-2-butene may then be reacted with water to form 2-trifluoromethyl-1,1,1-trifluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1-trifluoro-2-pentanol may be prepared by fluorinating commercially available 2-pentenal to form 1,1,2,3-tetrafluoropentane which may then be dehydrogenated to form 1,1-difluoro-1-pentene. CF.sub.3 may then be reacted with the 1,1-difluoro-1-pentene to form 2-trifluoromethyl-1,1,1-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,1-trifluoro-2-pentene. The 2-trifluoromethyl-1,1,1-trifluoro-2-pentene may then be reacted with water to form 2-trifluoromethyl-1,1,1-trifluoro-2-pentanol.

The present compounds are useful as solvents for use in vapor degreasing and other solvent cleaning applications including defluxing, cold cleaning, dry cleaning, dewatering, decontamination, spot cleaning, aerosol propelled rework, extraction, particle removal, and surfactant cleaning applications. These compounds are also useful as blowing agents, Rankine cycle and absorption refrigerants, and power fluids and especially as refrigerants for centrifugal refrigeration chillers.

The present invention also provides a method of cleaning a solid surface which comprises treating the surface with a compound having the Formula: ##STR3## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms.

Preferably, R' in the Formula above is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, CH.sub.3, CF.sub.3 CF.sub.2 --, CF.sub.3 (CF.sub.2).sub.2 --, CF.sub.3 CF.sub.2 CHF--, CF.sub.3 CF.sub.2 CH.sub.2 --, CF.sub.3 CHF--, CF.sub.3 (CHF).sub.2 --, CF.sub.3 CHFCF.sub.2 --, CF.sub.3 CHFCH.sub.2 --, CF.sub.3 CH.sub.2 --, CF.sub.3 (CH.sub.2).sub.2 --, CF.sub.3 CH.sub.2 CF.sub.2 --, CF.sub.3 CH.sub.2 CHF--, CHF.sub.2 CF.sub.2 --, CHF.sub.2 (CF.sub.2).sub.2 --, CHF.sub.2 CF.sub.2 CHF--, CHF.sub.2 CF.sub.2 CH.sub.2 --, CHF.sub.2 CHF--, CHF.sub.2 (CHF).sub.2 --, CHF.sub.2 CHFCF.sub.2 --, CHF.sub.2 CHFCH.sub.2 --, CHF.sub.2 CH.sub.2 --, CHF.sub.2 (CH.sub.2).sub.2 --, CHF.sub.2 CH.sub.2 CF.sub.2 --, CHF.sub.2 CH.sub.2 CHF--, CH.sub.2 FCF.sub.2 --, CH.sub.2 F(CF.sub.2).sub.2 --, CH.sub.2 FCF.sub. 2 CHF--, CH.sub.2 FCF.sub.2 CH.sub.2 --, CH.sub.2 FCHF--, CH.sub.2 F(CHF).sub.2 --, CH.sub.2 FCHFCF.sub.2 --, CH.sub.2 FCHFCH.sub.2 --, CH.sub.2 FCH.sub.2 --, CH.sub.2 F(CH.sub.2).sub.2 --, CH.sub.2 FCH.sub.2 CF.sub.2 --, CH.sub.2 FCH.sub.2 CHF--, CH.sub.3 CF.sub.2 --, CH.sub.3 (CF.sub.2).sub.2 --, CH.sub.3 CF.sub.2 CHF--, CH.sub.3 CF.sub.2 CH.sub.2 --, CH.sub.3 CHF--, CH.sub.3 (CHF).sub.2 --, CH.sub.3 CHFCF.sub.2 --, CH.sub.3 CHFCH.sub.2 --, CH.sub.3 CH.sub.2 --, CH.sub.3 (CH.sub.2).sub.2 --, CH.sub.3 (CH.sub.2).sub.3 --, CH.sub.3 CH.sub.2 CF.sub.2 --, CH.sub.3 (CH.sub.2).sub.2 CF.sub.2 --, CH.sub.3 (CH.sub.2).sub.3 CF.sub.2 --, CH.sub.3 CH.sub.2 (CF.sub.2).sub.2 --, CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2 --, and CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2 --.

In the process embodiment of the invention, the compositions may be used to clean solid surfaces by treating the surfaces with the compounds in any manner well known to the art such as by dipping or spraying or use of conventional degreasing apparatus.

When the novel compounds are used to clean solid surfaces by spraying the surfaces with the compounds, preferably, the novel compounds are sprayed onto the surfaces by using a propellant. Preferably, the propellant is selected from the group consisting of hydrochlorofluorocarbon, hydrofluorocarbon, and mixtures thereof. Useful hydrochlorofluorocarbon propellants include dichlorofluoromethane (known in the art as HCFC-21), chlorodifluoromethane (known in the art as HCFC-22), 1,1-dichloro-2,2-difluoroethane (known in the art as HCFC-132a), 1-chloro-2,2,2-trifluoroethane (known in the art as HCFC-133), and 1-chloro-1,1-difluoroethane (known in the art as HCFC-142b); commercially available HCFC-21, HCFC-22, and HCFC-142b may be used in the present invention. Useful hydrofluorocarbon propellants include trifluoromethane (known in the art as HFC-23), 1,1,1,2-tetrafluoroethane (known in the art as HFC-134a), and 1,1-difluoroethane (known in the art as HFC-152a): commercially available HFC-23 and HFC-152a may be used in the present invention. Until HFC-134a becomes available in commercial quantities, HFC-134a may be made by a known method such as that disclosed by U.S. Pat. No. 4,851,595. Preferred propellants include chlorodifluoromethane and 1,1,1,2-tetrafluoroethane. The present invention is more fully illustrated by the following non-limiting Examples.

EXAMPLES 1-573

For each example, the novel compound of the Formula above having the R and R' groups as indicated in Table I below is made.

TABLE I______________________________________Example R R"______________________________________ 1 CF.sub.3, CHF.sub.2 CF.sub.3 2 CF.sub.3, CHF.sub.2 CHF.sub.2 3 CF.sub.3, CHF.sub.2 CH.sub.2 F 4 CF.sub.3, CHF.sub.2 CH.sub.3 5 CF.sub.3, CHF.sub.2 CF.sub.3 CF.sub.2 6 CF.sub.3, CHF.sub.2 CF.sub.3 (CF.sub.2).sub.2 7 CF.sub.3, CHF.sub.2 CF.sub.3 CF.sub.2 CHF 8 CF.sub.3, CHF.sub.2 CF.sub.3 CF.sub.2 CH.sub.2 9 CF.sub.3, CHF.sub.2 CF.sub.3 CHF 10 CF.sub.3, CHF.sub.2 CF.sub.3 (CHF).sub.2 11 CF.sub.3, CHF.sub.2 CF.sub.3 CHFCF.sub.2 12 CF.sub.3, CHF.sub.2 CF.sub.3 CHFCH.sub.2 13 CF.sub.3, CHF.sub.2 CF.sub.3 CH.sub.2 14 CF.sub.3, CHF.sub.2 CF.sub.3 (CH.sub.2).sub.2 15 CF.sub.3, CHF.sub.2 CF.sub.3 CH.sub.2 CF.sub.2 16 CF.sub.3, CHF.sub.2 CF.sub.3 CH.sub.2 CHF 17 CF.sub.3, CHF.sub.2 CHF.sub.2 CF.sub.2 18 CF.sub.3, CHF.sub.2 CHF.sub.2 (CF.sub.2).sub.2 19 CF.sub.3, CHF.sub.2 CHF.sub.2 CF.sub.2 CHF 20 CF.sub.3, CHF.sub.2 CHF.sub.2 CF.sub.2 CH.sub.2 21 CF.sub.3, CHF.sub.2 CHF.sub.2 CHF 22 CF.sub.3, CHF.sub.2 CHF.sub.2 (CHF).sub.2 23 CF.sub.3, CHF.sub.2 CHF.sub.2 CHFCF.sub.2 24 CF.sub.3, CHF.sub.2 CHF.sub.2 CHFCH.sub.2 25 CF.sub.3, CHF.sub.2 CHF.sub.2 CH.sub.2 26 CF.sub.3, CHF.sub.2 CHF.sub.2 (CH.sub.2).sub.2 27 CF.sub.3, CHF.sub.2 CHF.sub.2 CH.sub.2 CF.sub.2 28 CF.sub.3, CHF.sub.2 CHF.sub.2 CH.sub.2 CHF 29 CF.sub.3, CHF.sub.2 CH.sub.2 FCF.sub.2 30 CF.sub.3, CHF.sub.2 CH.sub.2 F(CF.sub.2).sub.2 31 CF.sub.3, CHF.sub.2 CH.sub.2 FCF.sub.2 CHF 32 CF.sub.3, CHF.sub.2 CH.sub.2 FCF.sub.2 CH.sub.2 33 CF.sub.3, CHF.sub.2 CH.sub.2 FCHF 34 CF.sub.3, CHF.sub.2 CH.sub.2 (CHF).sub.2 35 CF.sub.3, CHF.sub.2 CH.sub.2 FCHFCF.sub.2 36 CF.sub.3, CHF.sub.2 CH.sub.2 FCHFCH.sub.2 37 CF.sub.3, CHF.sub.2 CH.sub.2 FCH.sub.2 38 CF.sub.3, CHF.sub.2 CH.sub.2 F(CH.sub.2).sub.2 39 CF.sub.3, CHF.sub.2 CH.sub.2 FCH.sub.2 CF.sub.2 40 CF.sub.3, CHF.sub.2 CH.sub.2 FCH.sub.2 CHF 41 CF.sub.3, CHF.sub.2 CH.sub.3 CF.sub.2 42 CF.sub.3, CHF.sub.2 CH.sub.3 (CF.sub.2).sub.2 43 CF.sub.3, CHF.sub.2 CH.sub.3 CF.sub.2 CHF 44 CF.sub.3, CHF.sub.2 CH.sub.3 CF.sub.2 CH.sub.2 45 CF.sub.3, CHF.sub.2 CH.sub.3 CHF 46 CF.sub.3, CHF.sub.2 CH.sub.3 (CHF).sub.2 47 CF.sub.3, CHF.sub.2 CH.sub.3 CHFCF.sub.2 48 CF.sub.3, CHF.sub.2 CH.sub.3 CHFCH.sub.2 49 CF.sub.3, CHF.sub.2 CH.sub.3 CH.sub.2 CF.sub.2 50 CF.sub.3, CHF.sub.2 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2 51 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2)CF.sub.2 CF.sub.2 52 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2 53 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2 54 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2 55 CF.sub.3, CH.sub.2 F CF.sub.3 56 CF.sub.3, CH.sub.2 F CHF.sub.2 57 CF.sub.3, CH.sub.2 F CH.sub.2 F 58 CF.sub.3, CH.sub.2 F CH.sub.3 59 CF.sub. 3, CH.sub.2 F CF.sub.3 CF.sub.2 60 CF.sub.3, CH.sub.2 F CF.sub.3 (CF.sub.2).sub.2 61 CF.sub.3, CH.sub.2 F CF.sub.3 CF.sub.2 CHF 62 CF.sub.3, CH.sub.2 F CF.sub.3 CF.sub.2 CH.sub.2 63 CF.sub.3, CH.sub.2 F CF.sub.3 CHF 64 CF.sub.3, CH.sub.2 F CF.sub.3 (CHF).sub.2 65 CF.sub.3, CH.sub.2 F CF.sub.3 CHFCF.sub.2 66 CF.sub.3, CH.sub.2 F CF.sub.3 CHFCH.sub.2 67 CF.sub.3, CH.sub.2 F CF.sub.3 CH.sub.2 68 CF.sub.3, CH.sub.2 F CF.sub.3 (CH.sub.2).sub.2 69 CF.sub.3, CH.sub.2 F CF.sub.3 CH.sub.2 CF.sub.2 70 CF.sub.3, CH.sub.2 F CF.sub.3 CH.sub.2 CHF 71 CF.sub.3, CH.sub.2 F CHF.sub.2 CF.sub.2 72 CF.sub.3, CH.sub.2 F CHF.sub.2 (CF.sub.2).sub.2 73 CF.sub.3, CH.sub.2 F CHF.sub.2 CF.sub.2 CHF 74 CF.sub.3, CH.sub.2 F CHF.sub.2 CF.sub.2 CH.sub.2 75 CF.sub.3, CH.sub.2 F CHF.sub.2 CHF 76 CF.sub.3, CH.sub.2 F CHF.sub.2 (CHF).sub.2 77 CF.sub.3, CH.sub.2 F CHF.sub.2 CHFCF.sub.2 78 CF.sub.3, CH.sub.2 F CHF.sub.2 CHFCH.sub.2 79 CF.sub.3, CH.sub.2 F CHF.sub.2 CH.sub.2 80 CF.sub.3, CH.sub.2 F CHF.sub.2 (CH.sub.2).sub.2 81 CF.sub.3, CH.sub.2 F CHF.sub.2 CH.sub.2 CF.sub.2 82 CF.sub.3, CH.sub.2 F CHF.sub.2 CH.sub.2 CHF 83 CF.sub.3, CH.sub.2 F CHF.sub.2 FCF.sub.2 84 CF.sub.3, CH.sub.2 F CH.sub.2 F(CF.sub.2).sub.2 85 CF.sub.3, CH.sub.2 F CH.sub.2 FCF.sub.2 CHF 86 CF.sub.3, CH.sub.2 F CH.sub.2 FCF.sub.2 CH.sub.2 87 CF.sub.3, CH.sub.2 F CH.sub.2 FCHF 88 CF.sub.3, CH.sub.2 F CH.sub.2 (CHF).sub.2 89 CF.sub.3, CH.sub.2 F CH.sub.2 FCHFCF.sub.2 90 CF.sub.3, CH.sub.2 F CH.sub.2 FCHFCH.sub.2 91 CF.sub.3, CH.sub.2 F CH.sub.2 FCH.sub.2 92 CF.sub.3, CH.sub.2 F CH.sub.2 F(CH.sub.2).sub.2 93 CF.sub.3, CH.sub.2 F CH.sub.2 FCH.sub.2 CF.sub.2 94 CF.sub.3, CH.sub.2 F CH.sub.2 FCH.sub.2 CHF 95 CF.sub.3, CH.sub.2 F CH.sub.3 CF.sub.2 96 CF.sub.3, CH.sub.2 F CH.sub.3 (CF.sub.2).sub.2 97 CF.sub.3, CH.sub.2 F CH.sub.3 CF.sub.2 CHF 98 CF.sub.3, CH.sub.2 F CH.sub.3 CF.sub.2 CH.sub.2 99 CF.sub.3, CH.sub.2 F CH.sub.3 CHF100 CF.sub.3, CH.sub.2 F CH.sub.3 (CHF).sub.2101 CF.sub.3, CH.sub.2 F CH.sub.3 CHFCF.sub.2102 CF.sub.3, CH.sub.2 F CH.sub.3 CHFCH.sub.2103 CF.sub.3, CH.sub.2 F CH.sub.3 CH.sub.2 CF.sub.2104 CF.sub.3, CH.sub.2 F CH.sub.3 CH.sub.2 (CF.sub.2).sub.2105 CF.sub.3, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2 CF.sub.2106 CF.sub.3, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2107 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CH.sub.2 F, CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2 CF.sub.2298 CH.sub.2 F, CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2 CHF299 CH.sub.2 F, CH.sub.3 CF.sub.2 CHF.sub.2 FCF.sub.2300 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 F(CF.sub.2).sub.2301 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2 CHF302 CH.sub. 2 F, CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2 CH.sub.2303 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 FCHF304 CH.sub.2 F, CH.sub.3 CF.sub.2 CHF.sub.2 (CHF).sub.2305 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 FCHFCF.sub.2306 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 FCHFCH.sub.2307 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2308 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 F(CH.sub.2).sub.2309 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2 CF.sub.2310 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2 CHF311 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2312 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 (CF.sub.2).sub.2313 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2 CHF314 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2 CH.sub.2315 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CHF316 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 (CHF).sub.2317 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CHFCF.sub.2318 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CHFCH.sub.2319 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2 CF.sub.2320 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2321 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2 CF.sub.2322 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2323 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2324 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2325 CF.sub.3, CF.sub.3 CF.sub.3326 CF.sub.3, CF.sub.3 CHF.sub.2327 CF.sub.3, CF.sub.3 CH.sub.2 F328 CF.sub.3, CF.sub.3 CH.sub.3329 CF.sub.3, CF.sub.3 CF.sub. 3 CF.sub.2330 CF.sub.3, CF.sub.3 CF.sub.3 (CF.sub.2).sub.2331 CF.sub.3, CF.sub.3 CF.sub.3 CF.sub.2 CHF332 CF.sub.3, CF.sub.3 CF.sub.3 CF.sub.2 CH.sub.2333 CF.sub.3, CF.sub.3 CF.sub.3 CHF334 CF.sub.3, CF.sub.3 CF.sub.3 (CHF).sub.2335 CF.sub.3, CF.sub.3 CF.sub.3 CHFCF.sub.2336 CF.sub.3, CF.sub.3 CF.sub.3 CHFCH.sub.2337 CF.sub.3, CF.sub.3 CF.sub.3 CH.sub.2338 CF.sub.3, CF.sub.3 CF.sub.3 (CH.sub.2).sub.2339 CF.sub.3, CF.sub.3 CF.sub.3 CH.sub.2 CF.sub.2340 CF.sub.3, CF.sub.3 CF.sub.3 CH.sub.2 CHF341 CF.sub.3, CF.sub.3 CHF.sub.2 CF.sub.2342 CF.sub.3, CF.sub.3 CHF.sub.2 (CF.sub.2).sub.2343 CF.sub.3, CF.sub.3 CHF.sub.2 CF.sub.2 CHF344 CF.sub.3, CF.sub.3 CHF.sub.2 CF.sub.2 CH.sub.2345 CF.sub.3, CF.sub.3 CHF.sub.2 CHF346 CF.sub.3, CF.sub.3 CHF.sub.2 (CHF).sub.2347 CF.sub.3, CF.sub.3 CHF.sub.2 CHFCF.sub.2348 CF.sub.3, CF.sub.3 CHF.sub.2 CHFCH.sub.2349 CF.sub.3, CF.sub.3 CHF.sub.2 CH.sub.2350 CF.sub.3, CF.sub.3 CHF.sub.2 (CH.sub.2).sub.2351 CF.sub.3, CF.sub.3 CHF.sub.2 CH.sub.2 CF.sub.2352 CF.sub.3, CF.sub.3 CHF.sub.2 CH.sub.2 CHF353 CF.sub.3, CF.sub.3 CHF.sub.2 FCF.sub.2354 CF.sub.3, CF.sub.3 CH.sub.2 F(CF.sub.2).sub.2355 CF.sub.3, CF.sub.3 CH.sub.2 FCF.sub.2 CHF356 CF.sub.3, CF.sub.3 CH.sub.2 FCF.sub.2 CH.sub.2357 CF.sub.3, CF.sub.3 CH.sub.2 FCHF358 CF.sub.3, CF.sub.3 CHF.sub.2 (CHF).sub.2359 CF.sub.3, CF.sub.3 CH.sub.2 FCHFCF.sub.2360 CF.sub.3, CF.sub.3 CH.sub.2 FCHFCH.sub.2361 CF.sub.3, CF.sub.3 CH.sub.2 FCH.sub. 2362 CF.sub.3, CF.sub.3 CH.sub.2 F(CH.sub.2).sub.2363 CF.sub.3, CF.sub.3 CH.sub.2 FCH.sub.2 CF.sub.2364 CF.sub.3, CF.sub.3 CH.sub.2 FCH.sub.2 CHF365 CF.sub.3, CF.sub.3 CH.sub.3 CF.sub.2366 CF.sub.3, CF.sub.3 CH.sub.3 (CF.sub.2).sub.2367 CF.sub.3, CF.sub.3 CH.sub.3 CF.sub.2 CHF368 CF.sub.3, CF.sub.3 CH.sub.3 CF.sub.2 CH.sub.2369 CF.sub.3, CF.sub.3 CH.sub.3 CHF370 CF.sub.3, CF.sub.3 CH.sub.3 (CHF).sub.2371 CF.sub.3, CF.sub.3 CH.sub.3 CHFCF.sub.2372 CF.sub.3, CF.sub.3 CH.sub.3 CHFCH.sub.2373 CF.sub.3, CF.sub.3 CH.sub.3 CH.sub.2 CF.sub.2374 CF.sub.3, CF.sub.3 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2375 CF.sub.3, CF.sub.3 CH.sub.3 (CH.sub.2).sub.2 CF.sub.2376 CF.sub.3, CF.sub.3 CH.sub.3 (CH.sub.2).sub.2 (CF.sub. 2).sub.2377 CF.sub.3, CF.sub.3 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2378 CF.sub.3, CF.sub.3 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2379 CHF.sub.2, CHF.sub.2 CF.sub.3380 CHF.sub.2, CHF.sub.2 CHF.sub.2381 CHF.sub.2, CHF.sub.2 CH.sub.2 F382 CHF.sub.2, CHF.sub.2 CH.sub.3383 CHF.sub.2, CHF.sub.2 CF.sub.3 CF.sub.2384 CHF.sub.2, CHF.sub.2 CF.sub.3 (CF.sub.2).sub.2385 CHF.sub.2, CHF.sub.2 CF.sub.3 CF.sub.2 CHF386 CHF.sub.2, CHF.sub.2 CF.sub.3 CF.sub.2 CH.sub.2387 CHF.sub.2, CHF.sub.2 CF.sub.3 CHF388 CHF.sub.2, CHF.sub.2 CF.sub.3 (CHF).sub.2389 CHF.sub.2, CHF.sub.2 CF.sub.3 CHFCF.sub.2390 CHF.sub.2, CHF.sub.2 CF.sub.3 CHFCH.sub.2391 CHF.sub.2, CHF.sub.2 CF.sub.3 CH.sub.2392 CHF.sub.2, CHF.sub.2 CF.sub.3 (CH.sub.2).sub. 2393 CHF.sub.2, CHF.sub.2 CF.sub.3 CH.sub.2 CF.sub.2394 CHF.sub.2, CHF.sub.2 CF.sub.3 CH.sub.2 CHF395 CHF.sub.2, CHF.sub.2 CHF.sub.2 CF.sub.2396 CHF.sub.2, CHF.sub.2 CHF.sub.2 (CF.sub.2).sub.2397 CHF.sub.2, CHF.sub.2 CHF.sub.2 CF.sub.2 CHF398 CHF.sub.2, CHF.sub.2 CHF.sub.2 CF.sub.2 CH.sub.2399 CHF.sub.2, CHF.sub.2 CHF.sub.2 CHF400 CHF.sub.2, CHF.sub.2 CHF.sub.2 (CHF).sub.2401 CHF.sub.2, CHF.sub.2 CHF.sub.2 CHFCF.sub.2402 CHF.sub.2, CHF.sub.2 CHF.sub.2 CHFCH.sub.2403 CHF.sub.2, CHF.sub.2 CHF.sub.2 CH.sub.2404 CHF.sub.2, CHF.sub.2 CHF.sub.2 (CH.sub.2).sub.2405 CHF.sub.2, CHF.sub.2 CHF.sub.2 CH.sub.2 CF.sub.2406 CHF.sub.2, CHF.sub.2 CHF.sub.2 CH.sub.2 CHF407 CHF.sub.2, CHF.sub.2 CHF.sub.2 FCF.sub.2408 CHF.sub.2, CHF.sub.2 CH.sub.2 F(CF.sub. 2).sub.2409 CHF.sub.2, CHF.sub.2 CH.sub.2 FCF.sub.2 CHF410 CHF.sub.2, CHF.sub.2 CH.sub.2 FCF.sub.2 CH.sub.2411 CHF.sub.2, CHF.sub.2 CH.sub.2 FCHF412 CHF.sub.2, CHF.sub.2 CHF.sub.2 (CHF).sub.2413 CHF.sub.2, CHF.sub.2 CH.sub.2 FCHFCF.sub.2414 CHF.sub.2, CHF.sub.2 CH.sub.2 FCHFCH.sub.2415 CHF.sub.2, CHF.sub.2 CH.sub.2 FCH.sub.2416 CHF.sub.2, CHF.sub.2 CH.sub.2 F(CH.sub.2).sub.2417 CHF.sub.2, CHF.sub.2 CH.sub.2 FCH.sub.2 CF.sub.2418 CHF.sub.2, CHF.sub.2 CH.sub.2 FCH.sub.2 CHF419 CHF.sub.2, CHF.sub.2 CH.sub.3 CF.sub.2420 CHF.sub.2, CHF.sub.2 CH.sub.3 (CF.sub.2).sub.2421 CHF.sub.2, CHF.sub.2 CH.sub.3 CF.sub.2 CHF422 CHF.sub.2, CHF.sub.2 CH.sub.3 CF.sub.2 CH.sub.2423 CHF.sub.2, CHF.sub.2 CH.sub.3 CHF424 CHF.sub.2, CHF.sub.2 CH.sub.3 (CHF).sub. 2425 CHF.sub.2, CHF.sub.2 CH.sub.3 CHFCF.sub.2426 CHF.sub.2, CHF.sub.2 CH.sub.3 CHFCH.sub.2427 CHF.sub.2, CHF.sub.2 CH.sub.3 CH.sub.2 CF.sub.2428 CHF.sub.2, CHF.sub.2 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2429 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.2 CF.sub.2430 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2431 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2432 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2433 CH.sub.2, CHF.sub.2 F CF.sub.3434 CH.sub.2, CHF.sub.2 F CHF.sub.2435 CH.sub.2, CHF.sub.2 F CH.sub.2 F436 CH.sub.2, CHF.sub.2 F CH.sub.3437 CH.sub.2, CHF.sub.2 F CF.sub.3 CF.sub.2438 CH.sub.2, CHF.sub.2 F CF.sub.3 (CF.sub.2).sub.2439 CH.sub.2, CHF.sub.2 F CF.sub.3 CF.sub. 2 CHF440 CH.sub.2, CHF.sub.2 F CF.sub.3 CF.sub.2 CH.sub.2441 CH.sub.2, CHF.sub.2 F CF.sub.3 CHF442 CH.sub.2, CHF.sub.2 F CF.sub.3 (CHF).sub.2443 CH.sub.2, CHF.sub.2 F CF.sub.3 CHFCF.sub.2444 CH.sub.2, CHF.sub.2 F CF.sub.3 CHFCH.sub.2445 CH.sub.2, CHF.sub.2 F CF.sub.3 CH.sub.2446 CH.sub.2, CHF.sub.2 F CF.sub.3 (CH.sub.2).sub.2447 CH.sub.2, CHF.sub.2 F CF.sub.3 CH.sub.2 CF.sub.2448 CH.sub.2, CHF.sub.2 F CF.sub.3 CH.sub.2 CHF449 CH.sub.2, CHF.sub.2 F CHF.sub.2 CF.sub.2450 CH.sub.2, CHF.sub.2 F CHF.sub.2 (CF.sub.2).sub.2451 CH.sub.2, CHF.sub.2 F CHF.sub.2 CF.sub.2 CHF452 CH.sub.2, CHF.sub.2 F CHF.sub.2 CF.sub.2 CH.sub.2453 CH.sub.2, CHF.sub.2 F CHF.sub.2 CHF454 CH.sub.2, CHF.sub.2 F CHF.sub.2 (CHF).sub.2455 CH.sub.2, CHF.sub.2 F CHF.sub.2 CHFCF.sub.2456 CH.sub.2, CHF.sub.2 F CHF.sub.2 CHFCH.sub.2457 CH.sub.2, CHF.sub.2 F CHF.sub.2 CH.sub.2458 CH.sub.2, CHF.sub.2 F CHF.sub.2 (CH.sub.2).sub.2459 CH.sub.2, CHF.sub.2 F CHF.sub.2 CH.sub.2 CF.sub.2460 CH.sub.2, CHF.sub.2 F CHF.sub.2 CH.sub.2 CHF461 CH.sub.2, CHF.sub.2 F CHF.sub.2 FCF.sub.2462 CH.sub.2, CHF.sub.2 F CH.sub.2 F(CF.sub.2).sub.2463 CH.sub.2, CHF.sub.2 F CH.sub.2 FCF.sub.2 CHF464 CH.sub.2, CHF.sub.2 F CH.sub.2 FCF.sub.2 CH.sub.2465 CH.sub.2, CHF.sub.2 F CH.sub.2 FCHF466 CH.sub.2, CHF.sub.2 F CHF.sub.2 (CHF).sub.2467 CH.sub.2, CHF.sub.2 F CH.sub.2 FCHFCF.sub.2468 CH.sub.2, CHF.sub.2 F CH.sub.2 FCHFCH.sub.2469 CH.sub.2, CHF.sub.2 F CH.sub.2 FCH.sub.2470 CH.sub.2, CHF.sub.2 F CH.sub.2 F(CH.sub.2).sub.2471 CH.sub.2, CHF.sub.2 F CH.sub.2 FCH.sub.2 CF.sub. 2472 CH.sub.2, CHF.sub.2 F CH.sub.2 FCH.sub.2 CHF473 CH.sub.2, CHF.sub.2 F CH.sub.3 CF.sub.2474 CH.sub.2, CHF.sub.2 F CH.sub.3 (CF.sub.2).sub.2475 CH.sub.2, CHF.sub.2 F CH.sub.3 CF.sub.2 CHF476 CH.sub.2, CHF.sub.2 F CH.sub.3 CF.sub.2 CH.sub.2477 CH.sub.2, CHF.sub.2 F CH.sub.3 CHF478 CH.sub.2, CHF.sub.2 F CH.sub.3 (CHF).sub.2479 CH.sub.2, CHF.sub.2 F CH.sub.3 CHFCF.sub.2480 CH.sub.2, CHF.sub.2 F CH.sub.3 CHFCH.sub.2481 CH.sub.2, CHF.sub.2 F CH.sub.3 CH.sub.2 CF.sub.2482 CH.sub.2, CHF.sub.2 F CH.sub.3 CH.sub.2 (CF.sub.2).sub.2483 CH.sub.2, CHF.sub.2 F CH.sub.3 (CH.sub.2).sub.2 CF.sub.2484 CH.sub.2, CHF.sub.2 F CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2485 CH.sub.2, CHF.sub.2 F CH.sub.3 (CH.sub.2).sub.3 CF.sub.2486 CH.sub.2, CHF.sub.2 F CH.sub. 3 (CH.sub.2).sub.3 (CF.sub.2).sub.2487 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3488 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2489 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 F490 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3491 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 CF.sub.2492 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 (CF.sub.2).sub.2493 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 CF.sub.2 CHF494 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 CF.sub.2 CH.sub.2495 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 CHF496 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 (CHF).sub.2497 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 CHFCF.sub.2498 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 CHFCH.sub.2499 CH.sub.3 CF.sub. 2, CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2500 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 (CH.sub.2).sub.2501 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2 CF.sub.2502 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2 CHF503 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2504 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 (CF.sub.2).sub.2505 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2 CHF506 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2 CH.sub.2507 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CHF508 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 (CHF).sub.2509 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CHFCF.sub.2510 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CHFCH.sub.2511 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2512 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 (CH.sub.2).sub.2513 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2 CF.sub.2514 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2 CHF515 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 FCF.sub.2516 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 F(CF.sub.2).sub.2517 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2 CHF518 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2 CH.sub.2519 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 FCHF520 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CHF.sub.2 (CHF).sub.2521 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 FCHFCF.sub.2522 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 FCHFCH.sub.2523 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2524 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 F(CH.sub.2).sub.2525 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2 CF.sub.2526 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2 CHF527 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2528 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CF.sub.2).sub.2529 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2 CHF530 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2 CH.sub.2531 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CHF532 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CHF).sub.2533 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CHFCF.sub.2534 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CHFCH.sub.2535 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2 CF.sub.2536 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2537 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2 CF.sub.2538 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2539 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2540 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2541 CF.sub.3, CF.sub.3 CF.sub.3542 CF.sub.3, CF.sub.3 CF.sub.3 CF.sub.2543 CF.sub.3, CF.sub.3 CF.sub.3 (CF.sub.2).sub.2544 CF.sub.3, CHF.sub.2 CH.sub.3 CH.sub.2545 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.2546 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3547 CF.sub.3, CH.sub.2 F CH.sub.3 CH.sub.3548 CF.sub.3, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2549 CF.sub.3, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.3550 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2551 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2552 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3553 CHF.sub.2, CH.sub.2 F CH.sub.3 CH.sub.2554 CHF.sub.2, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2555 CHF.sub.2, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.3556 CHF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2557 CHF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2558 CHF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3559 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2560 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2561 CH.sub.2 F, CH.sub.3 CF.sub.2 CH.sub. 3 (CH.sub.2).sub.3562 CF.sub.3, CF.sub.3 CH.sub.3 CH.sub.2563 CF.sub.3, CF.sub.3 CH.sub.3 (CH.sub.2).sub.2564 CF.sub.3, CF.sub.3 CH.sub.3 (CH.sub.2).sub.3565 CHF.sub.2, CHF.sub.2 CH.sub.3 CH.sub.2566 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.2567 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3568 CH.sub.2 F, CH.sub.2 F CH.sub.3 CH.sub.2569 CH.sub.2 F, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2570 CH.sub.2 F, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.3571 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2572 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2573 CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3______________________________________

EXAMPLES 574-1,146

Metal coupons are soiled with various types of oil. The soiled metal coupons are immersed in the novel solvents of Table I above for a period of 15 seconds to 2 minutes, removed, and allowed to air dry. Upon visual inspection, the soil appears to be substantially removed.

EXAMPLES 1,147-1,719

Metal coupons are soiled with various types of oil. The soiled metal coupons are wiped with the novel solvents of Table I above and allowed to air dry. Upon visual inspection, the soil appears to be substantially removed.

Having described the invention in detail and by reference to preferred embodiments thereof, it will be apparent that modifications and variations are possible without departing from the scope of the invention defined in the appended claims.

Claims

1. A compound having the formula ##STR4## wherein R' is selected from the group consisting of CF.sub.3 CF.sub.2 CHF--, CF.sub.3 CHFCF.sub.2 --, CHF.sub.2 (CF.sub.2).sub.2 --, CF.sub.3 CF.sub.2 CH.sub.2 --, CF.sub.3 (CHF).sub.2 --, CF.sub.3 CH.sub.2 CF.sub.2 --, CHF.sub.2 CF.sub.2 CHF--, CHF.sub.2 CHFCF.sub.2 --, CH.sub. F(CF.sub.2).sub.2, CF.sub.3 CHFCH.sub.2 --, CF.sub.3 CH.sub.2 CHF--, CHF.sub.2 CF.sub.2 CH.sub.2 --, CHF.sub.2 (CHF).sub.2 --, CHF.sub.2 CH.sub.2 CF.sub.2 --, CH.sub.2 FCF.sub.2 CHF--, CH.sub.2 FCHFCF.sub.2 --, CH.sub.3 (CF.sub.2).sub.2 --, CF.sub.3 (CH.sub.2).sub.2 --, CHF.sub.2 CHFCH.sub.2 --, CHF.sub.2 CH.sub.2 CHF--, CH.sub.2 FCF.sub.2 CH.sub.2 --, CH.sub.2 F(CHF).sub.2 --, CH.sub.2 FCH.sub.2 CF.sub.2 --, CH.sub.3 CF.sub.2 CHF--, CH.sub.3 CHFCF.sub.2 --, CHF.sub.2 (CH.sub.2).sub.2 --, CH.sub.2 FCHFCH.sub.2 --, CH.sub.2 FCH.sub.2 CHF-- , CH.sub.3 CF.sub.2 CH.sub.2 --, CH.sub.3 (CHF).sub.2 --, CH.sub.3 CH.sub.2 CF.sub.2 --, CH.sub.2 F(CH.sub.2).sub.2 --, and CH.sub.3 CHFCH.sub.2 --.

2. 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol.